Director of Data & AI, Homebase
$230-273k
+ equity + bonus
Employee scheduling software for small businesses
Open for applications
Employee scheduling software for small businesses
1001+ employees
Open for applications
$230-273k
+ equity + bonus
1001+ employees
Company mission
To make local business teams unstoppable.
Role
Who you are
- 10+ years in data and/or AI/ML, with at least 5 years leading teams of 8+ across data engineering, data science, or applied AI
- Director-level leadership experience. You've managed managers, built orgs, and driven technical strategy at a company with real scale
- Deep technical fluency across the modern data stack (warehousing, orchestration, transformation, BI) and applied ML/AI (production ML systems, LLMs, experimentation platforms)
- Strong product instincts. You connect data and AI work to customer outcomes and business metrics, not just technical milestones
- AI-first mindset. You actively use AI to improve your own workflows and have led teams that ship AI-powered products. You stay current on frontier developments (LLMs, agentic systems, multimodal AI)
- Excellent communication. You translate complex technical concepts for non-technical stakeholders and build trust across the org
- Experience with modern data platforms such as Databricks, Snowflake, or similar. Familiarity with Unity Catalog, Airflow, dbt, and ML platforms (MLflow, Baseten, or equivalent) is a strong plus
- Hybrid commitment. You're based in or willing to relocate to the Toronto area and are energized by in-person collaboration Tues/Weds at our Toronto hub
- Even if you don’t meet 100% of the qualifications, we encourage you to apply!
Desirable
- Experience building data and AI orgs at a SaaS or marketplace company serving SMBs
- Background in establishing data-as-a-product disciplines (data contracts, semantic layers, data mesh concepts)
- Experience with experimentation platforms and causal inference at scale
What the job involves
- We’re looking for a Director, Data & AI to lead our Data Engineering, Data & ML Platform, Data Science, and Applied AI teams. You'll own the strategy, execution, and people leadership for a 20+ person org that powers everything from our data platform and analytics infrastructure to production ML models and AI-powered product experiences
- This is a high-impact leadership role at the intersection of data and AI. You'll set the technical vision for how Homebase uses data as a product—trustworthy, consistent, and accessible—while driving applied AI initiatives that directly shape customer outcomes. You'll partner closely with Product, Engineering, and GTM leadership to ensure data and AI capabilities accelerate Homebase's growth strategy
- Own the Data & AI strategy. Define and execute the technical roadmap across data engineering, data platform, data science, and applied AI. Align priorities to Homebase's product and business goals
- Lead and grow a 20+ person org. Manage managers and senior ICs across four sub-teams. Recruit, develop, and retain top talent. Build a culture of velocity, ownership, and craft excellence
- Drive data platform and infrastructure. Own the reliability, scalability, and governance of Homebase's data stack (Databricks, Unity Catalog, Airflow, dbt). Ensure data is a trusted, self-serve asset across the company
- Accelerate applied AI and ML in product. Partner with Product and Engineering to ship AI-powered features—from LLM-based assistants to recommendation systems and intelligent automation. Own the MLOps lifecycle from experimentation to production
- Drive data science rigor. Build experimentation frameworks, guardrail metrics, and evaluation pipelines that drive confident product decisions. Ensure models are reliable, fair, and cost-effective
- Champion AI fluency org-wide. Coach your leaders to enable their teams with AI tools and workflows. Drive adoption of AI-assisted development practices (agentic coding, AI-augmented analytics). Measure and share impact
- Set governance and standards. Define org-wide standards for data quality, model monitoring, data contracts, and responsible AI use. Be the authority on data architecture and AI governance
- Partner cross-functionally. Work with Product, Growth, GTM, Finance, and CX to understand their data and AI needs. Enable a hub-and-spoke model where your team empowers the entire org to work with data effectively
Application process
- Meet the Talent Acquisition team. Mavel W
- Meet the Hiring Manager, Andrea C
- Meet with Engineering Leadership
- Participate in a Technical Deep Dive
- Meet Cross-functional Partners
- Meet with the Chief Development Officer, Ankit B
- Background Check + Offer Stage
- Welcome to the team, Homie
Our take
Homebase provides employees and businesses with time tracking applications, with a range of other HR functionality built in. Homebase automates the process of managing employee scheduling and also helps companies improve internal communications.
The company contributes to the reduction of paperwork in an office by turning an array of devices into time clocks that track hours and overtime, while also providing payroll support. This makes it easier for companies to remain in sync, running a more efficient operation as a result.
Given that Homebase's customer base of small businesses is not able to pay a lot for its product, scale is the key driver in the company's future success. With over 100,000 customers already, its significant venture capital backing will ensure that the company will be able to grow (notably, it's investing in Canadian talent) to provide its services on a profitable scale.
Freddie
Company Specialist at Welcome to the Jungle
Insights
29% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Apr 2024
$60m
SERIES D
Nov 2021
$30m
GROWTH EQUITY VC
Total funding: $189m
Company benefits
- Stock Options
- Paid parental leave
- Generous paid time off options
- Offsites, customer days & social events
- Work from Anywhere Month
- Group health benefits coverage
- Group RRSP with employer match + TFSA
- Snacks + lunch on us at hub offices
- MasterClass at Work for ongoing learning
Company HQ
Yerba Buena, San Francisco, CA
Leadership
John Waldmann
(Founder & CEO)BA Political Science at Stanford. Associate at Boston Consulting Group, then KKR Capstone, before founding Homebase in 2014.
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